CN106957263B - Compound, colorant composition comprising the compound, and resin composition comprising the compound - Google Patents

Compound, colorant composition comprising the compound, and resin composition comprising the compound Download PDF

Info

Publication number
CN106957263B
CN106957263B CN201611042509.8A CN201611042509A CN106957263B CN 106957263 B CN106957263 B CN 106957263B CN 201611042509 A CN201611042509 A CN 201611042509A CN 106957263 B CN106957263 B CN 106957263B
Authority
CN
China
Prior art keywords
group
chemical formula
substituted
unsubstituted
present
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201611042509.8A
Other languages
Chinese (zh)
Other versions
CN106957263A (en
Inventor
朴钟镐
金圣勋
李多美
李修莲
李在容
梁承秦
柳璋铉
朴相均
金载骏
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
LG Chem Ltd
Original Assignee
LG Chem Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Publication of CN106957263A publication Critical patent/CN106957263A/en
Application granted granted Critical
Publication of CN106957263B publication Critical patent/CN106957263B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof
    • C07D215/32—Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/36—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B25/00—Quinophthalones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular compounds
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Mathematical Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)
  • Electroluminescent Light Sources (AREA)
  • Polymerisation Methods In General (AREA)
  • Graft Or Block Polymers (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention relates to a compound represented by chemical formula 1, a colorant composition comprising the compound, and a resin composition comprising the compound.

Description

Compound, colorant composition comprising the compound, and resin composition comprising the compound
Technical Field
This application claims priority and benefit to korean patent application No. 10-2015-.
The present invention relates to a novel compound, a colorant composition comprising the compound, and a resin composition comprising the compound.
Background
Recently, LED or OLED devices, which are not driven by liquid crystal but self-luminous, are often used as a light source of a Liquid Crystal Display (LCD) instead of the existing CCFL. When an LED or OLED is used as a light source, a separate color filter is not required because red, green, and blue light is emitted autonomously.
However, it is often not easy to determine or adjust the required color coordinates by using the light emitted by the LED or OLED light source. Further, when a color filter is manufactured using developed color materials (particularly pigments) by using a pigment dispersion method, a method of improving color purity, brightness, and contrast has reached an upper limit.
In order to overcome these problems and satisfy the required conditions, development of new color materials is required.
[ list of references ]
[ patent document ]
Korean patent application laid-open No. 2001-0009058
Disclosure of Invention
Technical problem
The present invention aims to provide a novel compound, a colorant composition comprising the compound, and a resin composition comprising the compound.
Technical scheme
An exemplary embodiment of the present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
Figure GDA0002043401260000021
In the chemical formula 1, the first and second,
y is a direct bond or CQ1Q2,
r1 to R14, Q1 and Q2 are the same as or different from each other, and each independently is hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amide group, a carboxyl group (-COOH), -OC (═ O) R' ", a sulfonic acid group (-SO)3H) Sulfonamide groupSubstituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted boryl, substituted or unsubstituted amine, substituted or unsubstituted arylphosphino, substituted or unsubstituted phosphinoxide, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or adjacent groups may be combined with each other to form a substituted or unsubstituted ring, and
r' "is a substituted or unsubstituted alkyl group.
Another exemplary embodiment of the present invention provides a colorant composition comprising the compound represented by chemical formula 1.
Yet another exemplary embodiment of the present invention provides a resin composition comprising the colorant composition.
Another exemplary embodiment of the present invention provides a photosensitive material prepared by using the above-described resin composition.
Still another exemplary embodiment of the present invention provides a color filter including the above photosensitive material.
Still another exemplary embodiment of the present invention provides a display device including the color filter described above.
Advantageous effects
According to an exemplary embodiment of the present invention, a higher color gamut, higher brightness, higher contrast, and the like may be achieved because the colorant composition including the compound represented by chemical formula 1 has excellent color characteristics, heat resistance, light resistance, and solvent resistance, and prevents re-agglomeration of fine-particle pigments and dyes or generation of foreign substances.
Drawings
Fig. 1 shows an absorption spectrum in the visible light region of a substrate made of the resin composition in example 1.
Fig. 2 shows an absorption spectrum in the visible light region of a substrate made of the resin composition in example 2.
Fig. 3 shows an absorption spectrum in the visible light region of a substrate made of the resin composition in example 3.
Detailed Description
Hereinafter, the present invention will be described in more detail.
An exemplary embodiment of the present invention provides a compound represented by chemical formula 1.
In the present invention, when a component "includes" one constituent element, unless specifically described otherwise, it is not meant to exclude another constituent element, but is meant to include another constituent element as well.
In the present invention, examples of the substituent will be described below, but the present invention is not limited thereto.
The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of substitution is not limited as long as the position is a position at which the hydrogen atom is substituted (i.e., a position at which the substituent may be substituted), and when two or more are substituted, the two or more substituents may be the same as or different from each other.
In the present invention, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the group consisting of: deuterium, halogen group, nitrile group, nitro group, imide group, amide group, carbonyl group, ester group, hydroxyl group, carboxyl group (-COOH), sulfonic group (-SO)3H) Sulfonamide, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, substituted or unsubstituted arylthio, substituted or unsubstituted alkylsulfonyl, substituted or unsubstituted arylsulfonyl, substituted or unsubstituted alkenyl, substituted or unsubstituted silyl, substituted or unsubstituted borylA substituted amino group, a substituted or unsubstituted arylphosphino group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or a substituent linked by two or more substituents among the above-exemplified substituents, or no substituent. For example, "a substituent to which two or more substituents are attached" may be a biphenyl group. That is, a biphenyl group may also be an aryl group and may be interpreted as a substituent with two phenyl groups attached.
In the present invention, in the case of the present invention,
Figure GDA0002043401260000041
means a moiety or binding moiety bonded to another substituent.
In the present invention, the halogen group may be fluorine, chlorine, bromine or iodine.
In the present invention, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 30. Specifically, the imide group may be a compound having the following structure, but is not limited thereto.
Figure GDA0002043401260000042
In the present invention, for the amide group, the nitrogen of the amide group may be substituted with the following substituent: hydrogen; a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms; or an aryl group having 6 to 30 carbon atoms. Specifically, the amide group may be a compound having the following structural formula, but is not limited thereto.
Figure GDA0002043401260000043
In the present invention, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 30. Specifically, the carbonyl group may be a compound having the following structure, but is not limited thereto.
Figure GDA0002043401260000051
In the present invention, the ester group may be an alkyl ester group in which the oxygen of the ester group is substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms; cycloalkyl ester groups in which the oxygen of the ester group is substituted by a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; or an aryl ester group in which the oxygen of the ester group is substituted with an aryl group having 6 to 30 carbon atoms. Specifically, the ester group may be a compound having the following structural formula, but is not limited thereto.
Figure GDA0002043401260000052
In the present invention, the sulfonamide group may be-SO2NR 'R ", R' and R" are the same or different from each other and may each be independently selected from: hydrogen, deuterium, halogen, a nitrile group, a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted straight or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
In the present invention, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30, and specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, pentyl, 2-ethylhexyl, 1-methylheptyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylhept, 2, 2-dimethylheptyl, 1-ethylpropyl, 1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.
In the present invention, the cycloalkyl group is not particularly limited, but preferred is a cycloalkyl group having 3 to 30 carbon atoms, and specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.
In the present invention, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples thereof include methoxy group, ethoxy group, n-propoxy group, isopropoxy group (isopropoxy group), isopropyloxy group (i-propyloxy group), n-butoxy group, isobutoxy group, t-butoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3-dimethylbutyloxy group, 2-ethylbutoxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, benzyloxy group, p-methylbenzyloxy group and the like, but are not limited thereto.
In the present invention, the amine group may be selected from-NH2Monoalkylamino group, dialkylamino group, N-alkylarylamino group, monoarylamino group, diarylamino group, N-arylheteroarylamino group, N-alkylheteroarylamino group, monoheteroarylamino group, and diheteroarylamino group, the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, anilino, naphthylamino, biphenylamino, anthracylamino, 9-methylanthrylamino, diphenylamino, dimethylanilino, N-phenylmethylanilino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrylamino, N-biphenylphenanthrylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrylfluorenylamino, N-biphenylfluorenylamino, and the like.
In the present invention, an N-alkylarylamino group means an amino group in which an alkyl group and an aryl group are substituted with N of the amino group.
In the present invention, N-arylheteroarylamine group means an amine group in which aryl and heteroaryl groups are substituted by N of the amine group.
In the present invention, N-alkylheteroarylamino means an amino group in which an alkyl group and a heteroarylamino group are substituted with N of the amino group.
In the present invention, the alkyl group in the monoalkylamino group, dialkylamino group, N-arylalkylamino group, alkylthio group, alkylsulfonyl group and N-alkylheteroarylamino group is the same as the above example of the alkyl group. Specifically, examples of the alkylthio group include methylthio, ethylthio, tert-butylthio, hexylthio, octylthio and the like, and examples of the alkylsulfonyl group include methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl and the like, but are not limited thereto.
In the present invention, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 30. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl, styryl and the like, but are not limited thereto.
In the present invention, specific examples of the silyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present invention, the boron group may be-BR100R101And R is100And R101May be the same as or different from each other, and may each be independently selected from the group consisting of hydrogen, deuterium, halogen, a nitrile group, a substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
In the present invention, specific examples of the phosphine oxide group include, but are not limited to, diphenylphosphineoxide group, dinaphthylphospheoxide group and the like.
In the present invention, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
When the aryl group is a monocyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 6 to 30. Specific examples of the monocyclic aryl group may include phenyl, biphenyl, terphenyl, and the like, but are not limited thereto.
When the aryl group is a polycyclic aryl group, the number of carbon atoms thereof is not particularly limited, but is preferably 10 to 30. Specific examples of the polycyclic aromatic group include naphthyl, anthryl, phenanthryl, triphenyl, pyrenyl, perylenyl, perylene, and the like,
Figure GDA0002043401260000072
A phenyl group, a fluorenyl group, and the like, but are not limited thereto.
In the present invention, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.
When the fluorenyl group is substituted, the fluorenyl group can be
Figure GDA0002043401260000073
And
Figure GDA0002043401260000081
and the like. However, the fluorenyl group is not limited thereto.
In the present invention, the "adjacent" group may mean: a substituent substituted with an atom directly bonded to an atom substituted with a corresponding substituent; a substituent located sterically closest to the corresponding substituent; or another substituent substituted with an atom substituted with the corresponding substituent. For example, two substituents substituted at the ortho position in the phenyl ring and two substituents substituted with the same carbon in the aliphatic ring can be construed as groups "adjacent" to each other.
In the present invention, the aryl group and the aryl group in the aryloxy group, the arylthio group, the arylsulfonyl group, the monoarylamino group, the diarylamino group, the N-arylalkylamino group, the N-arylheteroarylamino group, and the arylphosphino group are the same as in the above examples. Specifically, examples of the aryloxy group include phenoxy group, p-tolyloxy group, m-tolyloxy group, 3, 5-dimethyl-phenoxy group, 2,4, 6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthracenoxy group, 2-anthracenoxy group, 9-anthracenoxy group, 1-phenanthrenoxy group, 3-phenanthrenoxy group, 9-phenanthrenoxy group and the like, examples of the arylthio group include phenylthio group, 2-methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfonyl group include benzenesulfonyl group, p-toluenesulfonyl group and the like, but are not limited.
In the present invention, the heteroaryl group contains one or more atoms other than carbon (i.e., heteroatoms), and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, and the like. The number of carbon atoms thereof is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of heterocyclic groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Figure GDA0002043401260000082
Azolyl group,
Figure GDA0002043401260000083
Oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Figure GDA0002043401260000084
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isooxazolyl
Figure GDA0002043401260000085
Azolyl group,
Figure GDA0002043401260000086
Oxadiazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present invention, examples of the monoheteroarylamino group, the diheteroarylamino group, the N-arylheteroarylamino group and the N-alkylheteroarylamino group are the same as the above examples of the heteroaryl group.
In the present invention, in a substituted or unsubstituted ring formed by the combination of adjacent groups, "ring" means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
In the present invention, the ring means a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted heterocyclic ring.
In the present invention, the hydrocarbon ring may be an aromatic ring, an aliphatic ring, or a fused ring of an aromatic ring and an aliphatic ring, and may be selected from examples of cycloalkyl groups or aryl groups, except that the hydrocarbon ring is not monovalent.
In the present invention, the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of aryl groups, except that the aromatic ring is not monovalent.
In the present invention, the heterocyclic ring contains one or more atoms other than carbon (i.e., heteroatoms), and specifically, the heteroatoms may include one or more atoms selected from O, N, Se, S, and the like. The heterocyclic ring may be monocyclic or polycyclic, may be an aromatic ring, an aliphatic ring, or a fused ring of an aromatic ring and an aliphatic ring, and may be selected from examples of heteroaryl groups, except that the heterocyclic ring is not monovalent.
According to an exemplary embodiment of the present invention, chemical formula 1 may be represented by the following chemical formula 1-a or 1-b.
[ chemical formula 1-a ]
Figure GDA0002043401260000091
[ chemical formula 1-b ]
Figure GDA0002043401260000092
In chemical formulas 1-a and 1-b, R1 to R14, Q1 and Q2 are defined as those in chemical formula 1.
According to an exemplary embodiment of the present invention, in chemical formula 1, Q1 and Q2 are hydrogen.
According to an exemplary embodiment of the present invention, in chemical formula 1, R1 to R14 are the same as or different from each other, and are each independently hydrogen, a halogen group, a nitro group, a carboxyl group, an ester group, a hydroxyl group, -OC (═ O) R' ", a sulfonic acid group (— SO)3H) A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group.
R' "is a substituted or unsubstituted alkyl group.
R' "is methyl.
According to an exemplary embodiment of the present invention, in chemical formula 1, R1 to R14 are the same as or different from each other, and are each independently hydrogen, fluorine, chlorine, bromine, iodine, nitro, carboxyl, alkyl ester group, cycloalkyl ester group, aryl ester group, hydroxyl group, -OC (═ O) CH3Sulfonic acid group (-SO)3H) Methyl, t-butyl, methoxy, or phenyl.
According to an exemplary embodiment of the present invention, in chemical formula 1, R6 to R9 are the same as or different from each other, and are each independently hydrogen, a halogen group, a nitro group, a carboxyl group, an ester group, a hydroxyl group, -OC (═ O) R' ", a sulfonic acid group (— SO)3H) A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group.
According to an exemplary embodiment of the present invention, in chemical formula 1, R6 to R9 are the same as or different from each other, and are each independently hydrogen, fluorine, chlorine, bromine, iodine, nitro, carboxyl, alkyl ester group, cycloalkyl ester group, aryl ester group, hydroxyl group, -OC (═ O) CH3Sulfonic acid group (-SO)3H) Methyl, t-butyl, methoxy, or phenyl.
According to an exemplary embodiment of the present invention, in chemical formula 1, at least one of Q1, Q2, and R6 to R14 is combined with an adjacent group to each other to form a substituted or unsubstituted ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, at least one of Q1, Q2, and R6 to R14 and an adjacent group are combined with each other to form a substituted or unsubstituted aromatic ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, at least one of Q1, Q2, and R6 to R14, and an adjacent group are combined with each other to form a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, at least one of Q1, Q2, and R6 to R14 is combined with an adjacent group to each other to form an unsubstituted or nitro or sulfonic acid group (-SO)3H) A substituted benzene ring, or a naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R6 and R7 are combined with each other to form a substituted or unsubstituted aromatic ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R6 and R7 combine with each other to form a substituted or unsubstituted benzene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R6 and R7 are combined with each other to form a benzene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R7 and R8 are combined with each other to form a substituted or unsubstituted aromatic ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R7 and R8 combine with each other to form a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R7 and R8 are combined with each other to form an unsubstituted or nitro or sulfonic acid group (-SO)3H) A substituted benzene ring, or a naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, Q1 and R6 are combined with each other to form a substituted or unsubstituted aromatic ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, Q1 and R6 combine with each other to form a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, Q1 and R6 are combined with each other to form a benzene ring, or a naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, Q2 and R6 are combined with each other to form a substituted or unsubstituted aromatic ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, Q2 and R6 combine with each other to form a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, Q2 and R6 are combined with each other to form a benzene ring, or a naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R10 and R11 are combined with each other to form a substituted or unsubstituted aromatic ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R10 and R11 combine with each other to form a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R10 and R11 are combined with each other to form a benzene ring, or a naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R11 and R12 are combined with each other to form a substituted or unsubstituted aromatic ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R11 and R12 combine with each other to form a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R11 and R12 are combined with each other to form a benzene ring, or a naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R12 and R13 are combined with each other to form a substituted or unsubstituted aromatic ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R12 and R13 combine with each other to form a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R12 and R13 are combined with each other to form a benzene ring, or a naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R13 and R14 are combined with each other to form a substituted or unsubstituted aromatic ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R13 and R14 combine with each other to form a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring.
According to an exemplary embodiment of the present invention, in chemical formula 1, R13 and R14 are combined with each other to form a benzene ring, or a naphthalene ring.
According to an exemplary embodiment of the present invention, chemical formula 1 is represented by any one of the following chemical formulae 1-c to 1-n.
[ chemical formula 1-c ]
Figure GDA0002043401260000121
[ chemical formula 1-d ]
Figure GDA0002043401260000131
[ chemical formulas 1-e ]
Figure GDA0002043401260000132
[ chemical formula 1-f ]
Figure GDA0002043401260000133
[ chemical formula 1-g ]
Figure GDA0002043401260000134
[ chemical formula 1-h ]
Figure GDA0002043401260000141
[ chemical formula 1-i ]
Figure GDA0002043401260000142
[ chemical formula 1-j ]
Figure GDA0002043401260000143
[ chemical formula 1-k ]
Figure GDA0002043401260000144
[ chemical formula 1-l ]
Figure GDA0002043401260000151
[ chemical formula 1-m ]
Figure GDA0002043401260000152
[ chemical formula 1-n ]
Figure GDA0002043401260000153
In the chemical formulas 1-c to 1-n,
the definitions of R6 to R9, Q1 and Q2 are the same as those in chemical formula 1.
According to an exemplary embodiment of the present invention, chemical formula 1 is represented by any one of the following chemical formulae 1-1 to 1-37.
Figure GDA0002043401260000161
Figure GDA0002043401260000171
Figure GDA0002043401260000181
Figure GDA0002043401260000191
Figure GDA0002043401260000201
Figure GDA0002043401260000211
In the chemical formulae 1 to 25,
r is a substituted or unsubstituted alkyl, a substituted or unsubstituted cycloalkyl, or a substituted or unsubstituted aryl.
According to another exemplary embodiment of the present invention, in chemical formulas 1 to 25, R is a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
According to another exemplary embodiment of the present invention, in chemical formulas 1 to 25, R is an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aryl group having 6 to 12 carbon atoms.
Another exemplary embodiment of the present invention provides a colorant composition comprising the compound represented by chemical formula 1.
The colorant composition may further include at least one of a dye and a pigment in addition to the compound represented by chemical formula 1. For example, the colorant composition may further include only the compound represented by chemical formula 1, but may include the compound represented by chemical formula 1 and one or more dyes, or may include the compound represented by chemical formula 1 and one or more pigments, or may further include the compound represented by chemical formula 1, one or more dyes, and one or more pigments.
An exemplary embodiment of the present invention provides a resin composition including the colorant composition.
In an exemplary embodiment of the present invention, the resin composition may further include: a binder resin, a multifunctional monomer, a photoinitiator, and a solvent.
The binder resin is not particularly limited as long as the binder resin can exhibit physical properties such as strength and developability of a film manufactured by using the resin composition.
The binder resin may use a copolymer resin of a multifunctional monomer imparting mechanical strength and a monomer imparting alkali solubility, and may further include a binder commonly used in the art.
The polyfunctional monomer that imparts mechanical strength to the membrane may be any one or more of the following: unsaturated carboxylic acid ester, aromatic vinyl compound, unsaturated ether, unsaturated imide and acid anhydride.
Specific examples of the unsaturated carboxylic acid ester may be selected from benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiglycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxypropylglycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiglycol (meth) acrylate, p-nonylphenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxy glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropentyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, α -3-tribromodecyl methacrylate, α, 366326, α, and α.
Specific examples of the aromatic vinyl monomer may be selected from styrene, α -methylstyrene, (o, m, p) -vinyltoluene, (o, m, p) -methoxystyrene, and (o, m, p) -chlorostyrene, but are not limited thereto.
Specific examples of the unsaturated ether may be selected from the group consisting of vinyl methyl ether, vinyl ethyl ether and allyl glycidyl ether, but are not limited thereto.
Specific examples of the unsaturated imide may be selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide and N-cyclohexylmaleimide, but are not limited thereto.
Examples of the acid anhydride include anhydrous maleic acid, anhydrous methyl maleic acid, tetrahydrophthalic anhydride, and the like, but are not limited thereto.
The monomer imparting alkali solubility is not particularly limited as long as the monomer contains an acid group, and one or more selected from the group consisting of: for example, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethylmaleic acid, 5-norbornene-2-carboxylic acid, mono-2- ((meth) acryloyloxy) ethyl phthalate, mono-2- ((meth) acryloyloxy) ethyl succinate, and ω -carboxy polycaprolactone mono (meth) acrylate, but the monomer is not limited thereto.
According to an exemplary embodiment of the present invention, the acid value of the binder resin is 50KOH mg/g to 130KOHmg/g, and the weight average molecular weight is 1,000 to 50,000.
The polyfunctional monomer is a monomer for forming a photoresist phase by light, and specifically, may be one or a mixture of two or more selected from the following: propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 6-hexanediol diacrylate, 1, 6-hexanediol acrylate, tetraethylene glycol methacrylate, diphenoxyethanol diacrylate, trihydroxyethyl isocyanurate trimethacrylate, trimethylpropyl trimethacrylate, dipentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, and dipentaerythritol hexamethacrylate.
The photoinitiator is not particularly limited as long as the photoinitiator is an initiator that generates radicals to initiate crosslinking, but may be selected from, for example, acetophenone compounds, diimidazole compounds, triazine compounds, and oxime compounds.
Examples of the acetophenone compounds include: 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) one, 1-hydroxycyclohexylphenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholinyl-1-propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) -butan-1-one, methyl-2-morpholinyl-1-one, methyl-2-phenylpropan-1-one, methyl-2-hydroxy-2-methyl-1-one, methyl-2-hydroxy-2-propyl-1-one, 2- (4-bromo-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) -butan-1-one, 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinylpropan-1-one, and the like, but is not limited thereto.
Examples of bisimidazoles include: 2, 2-bis (2-chlorophenyl) -4,4',5,5' -tetraphenyl diimidazole, 2 '-bis (o-chlorophenyl) -4,4',5,5 '-tetrakis (3,4, 5-trimethoxyphenyl) -1,2' -diimidazole, 2 '-bis (2, 3-dichlorophenyl) -4,4',5,5 '-tetraphenyl diimidazole, 2' -bis (o-chlorophenyl) -4,4,5,5 '-tetraphenyl-1, 2' -diimidazole, etc., but not limited thereto.
Examples of triazines include: 3- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid, 1,1,3,3, 3-hexafluoroisopropyl-3- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoate, ethyl-2- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoate, 2-oxiranyl-2- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } acetate, cyclohexyl-2- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } acetate, Benzyl-2- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] thiophenyl } -acetate, 3- { chloro-4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] thiophenyl } propanoic acid, 2, 4-bis (trichloromethyl) -6-p-methoxystyryl-s-triazine, 2, 4-bis (trichloromethyl) -6- (1-p-dimethylaminophenyl) -1, 3-butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but are not limited thereto.
Examples of oximes include: 1, 2-octanedione-1- (4-thiophenyl) phenyl-2- (O-benzoyloxime) (CIBA-GEIGY Corp., CGI 124), ethanone-1- (9-ethyl) -6- (2-methylbenzoyl-3-yl) -1- (O-acetyloxime) (CGI 242), N-1919(Adeka Corporation), and the like, but is not limited thereto.
The solvent may be one or more selected from the group consisting of: acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1, 4-bis
Figure GDA0002043401260000241
An alkane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, ethylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1, 2-dichloroethane, 1,1, 1-trichloroethane, 1,1, 2-trichloroethylene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl-3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, ethyl cellosolve, ethyl acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether, but are not limited thereto.
According to an exemplary embodiment of the present invention, the content of the colorant composition is 0.1 to 60% by weight, the content of the binder resin is 1 to 60% by weight, the content of the photoinitiator is 0.1 to 20% by weight, and the content of the polyfunctional monomer is 0.1 to 50% by weight, based on the total weight of the solid content in the resin composition.
The total weight of the solid content means the sum of the total weights of the components other than the solvent in the resin composition. The basis of the weight% based on the solid content and the solid content of each component can be measured by a conventional analytical device used in the art such as liquid chromatography or gas chromatography.
According to an exemplary embodiment of the present invention, the resin composition further comprises one or two or more additives selected from the group consisting of: a photo-crosslinking sensitizer, a curing accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, a UV absorber, a dispersant and a leveling agent.
According to an exemplary embodiment of the present invention, the content of the additive is 0.1 to 20% by weight based on the total weight of the solid content in the resin composition.
As the photo-crosslinking sensitizer, one or more selected from the following may be used: benzophenone-based compounds such as benzophenone, 4, 4-bis (dimethylamino) benzophenone, 4, 4-bis (diethylamino) benzophenone, 2,4, 6-trimethylaminobenzophenone, methyl o-benzoylbenzoate, 3-dimethyl-4-methoxybenzophenone and 3,3,4, 4-tetrakis (t-butylperoxycarbonyl) benzophenone; fluorenones such as 9-fluorenone, 2-chloro-9-fluorenone, and 2-methyl-9-fluorenone; thioxanthone compounds such as thioxanthone, 2, 4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone and diisopropylthioxanthone; xanthone compounds such as xanthone and 2-methylxanthone; anthraquinones such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, tert-butylanthraquinone and 2, 6-dichloro-9, 10-anthraquinone; acridine compounds, such as 9-phenylacridine, 1, 7-bis (9-acridinyl) heptane, 1, 5-bis (9-acridinylpentane), and 1, 3-bis (9-acridinyl) propane; dicarbonyl compounds such as benzyl, 1,7, 7-trimethyl-bicyclo [2,2,1] hepta-2, 3-dione and 9, 10-phenanthrenequinone; phosphine oxide compounds such as 2,4, 6-trimethylbenzoyldiphenylphosphine oxide and bis (2, 6-dimethoxybenzoyl) -2,4, 4-trimethylpentylphosphine oxide; benzoate compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate and 2-n-butoxyethyl-4- (dimethylamino) benzoate; amino synergists, such as 2, 5-bis (4-diethylaminobenzylidene) cyclopentanone, 2, 6-bis (4-diethylaminobenzylidene) cyclohexanone and 2, 6-bis (4-diethylaminobenzylidene) -4-methyl-cyclopentanone; coumarins, such as 3, 3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7-methoxycoumarin, and 10, 10-carbonylbis [1,1,7, 7-tetramethyl-2, 3,6, 7-tetrahydro-1H, 5H,11H-Cl ] -benzopyrano [6,7,8-ij ] -quinolizin-11-one; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzylideneacetophenone; and 2-benzoylmethylene and 3-methyl-b-naphthothiazoline.
A curing accelerator is used to increase curing and mechanical strength, and specifically, one or more selected from the following may be used: 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenz
Figure GDA0002043401260000251
Oxazole, 2, 5-dimercapto-1, 3, 4-thiadiazole, 2-mercapto-4, 6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate).
As the adhesion promoter used in the invention, one or more selected from the following may be selected and used: methacryloyl silane coupling agents such as methacryloxypropyltrimethoxysilane, methacryloxypropyldimethoxysilane, methacryloxypropyltriethoxysilane, and methacryloxypropyldimethoxysilane, and as the alkyltrimethoxysilane, one or more selected from the group consisting of: octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane, etc.
The surfactant is a silicone-based surfactant or a fluorine-based surfactant, and specifically, as the silicone-based surfactant, BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307, BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK-354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, etc., manufactured by BYK-Chemie co, ltd., can be used, and as the fluorine-based surfactant, it is possible to use (bion, BYK, bydic, etc.), (r) manufactured by danippon & ltd. Manufactured F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446, F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, f-483, F-484, F-486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF1132, TF1027SF, TF-1441, TF-1442 and the like, but the surfactant is not limited thereto.
The antioxidant may be one or more selected from the group consisting of: hindered phenol type antioxidants, amine type antioxidants, thio type antioxidants and phosphine type antioxidants, but are not limited thereto.
Specific examples of the antioxidant include phosphoric acid-based heat stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate, hindered phenol-based primary antioxidants such as 2, 6-di-t-butyl-p-cresol, octadecyl-3- (4-hydroxy-3, 5-di-t-butylphenyl) propionate, tetrakis [ methylene-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ] methane, 1,3, 5-trimethyl-2, 4, 6-tris (3, 5-di-t-butyl-4-hydroxybenzyl) benzene, 3, 5-di-t-butyl-4-hydroxybenzyl-phosphite diethyl ester, 2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4 '-butylidene-bis (3-methyl-6-t-butylphenol), 4' -thiobis (3-methyl-6-t-butylphenol) or bis [3, 3-bis- (4 '-hydroxy-3' -t-butylphenol) butanoic acid ] diol esters, amine-based antioxidants such as phenyl- α -naphthylamine, phenyl-triphenylamine, N-phenylnaphthylamine, N-bis (4 '-butyldiphenylmethanephosphite, N' -thiodiphenyl-4-bis (3 '-butylphosphite), N-dodecylbenzenediamine, N' -butyldiphenyl-4-bis (3 '-butyldiphenyl) phosphite, N' -butyldiphenyl-4 '-butyldiphenyl-2, 4' -tetramethylthiuracyl) phosphite, N '-diphenyl-bis (3' -diphenyl) or bis (4-phenylthiodiphenyl phosphite, N '-dodecyldiphenyl-2, N' -diphenyl-2, 4 '-diphenyl-2' -diphenyl-2, 4 '-tert-phenyl) phosphite, 2, 4' -tert-butyl.
As the UV absorber, 2- (3-tert-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxybenzophenone, and the like can be used, but the UV absorber is not limited thereto, and those generally used in the art can be used.
Examples of the thermal polymerization inhibitor may include one or more selected from the group consisting of: p-anisole, hydroquinone, catechol, t-butylcatechol, N-nitrosophenylhydroxylamine ammonium salt, N-nitrosophenylhydroxylamine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyrrogarole, benzoquinone, 4-thiobis (3-methyl-6-t-butylphenol), 2-methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine, but are not limited thereto, and may include those generally known in the art.
The dispersant may be used by the following method: the dispersant is added to the inside of the pigment in a form in which the pigment is surface-treated in advance, or to the outside of the pigment. As the dispersant, a compound type, nonionic, anionic or cationic dispersant may be used, and examples thereof include fluorine type surfactants, ester type surfactants, cationic type surfactants, anionic type surfactants, amphoteric surfactants and the like. These may be used alone or in a combination of two or more thereof.
Specific examples of dispersants include one or more selected from the group consisting of: polyalkylene glycols and esters thereof, polyoxyalkylene polyols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, ester sulfonates, carboxylic esters, carboxylic salts, alkylamide alkylene oxide adducts, and alkylamines, but are not limited thereto.
The leveling agent may be polymeric or non-polymeric. Specific examples of the polymeric leveling agent include polyethyleneimine, polyamidoamine, and a reaction product of amine and epoxide, and specific examples of the non-polymeric leveling agent include non-polymeric sulfur-containing compounds and non-polymeric nitrogen-containing compounds, but the examples are not limited thereto, and those generally used in the art may be used.
An exemplary embodiment of the present invention provides a photosensitive material prepared by using the resin composition.
More specifically, the resin composition of the present invention is applied to a base material by an appropriate method to form a photosensitive material in the form of a film or a pattern.
The application method is not particularly limited, but a spray coating method, a roll coating method, a spin coating method, and the like can be used, and generally, a spin coating method is widely used. Further, an application film is formed, and then, in some cases, the residual solvent may be partially removed under reduced pressure.
Examples of the light source for curing the resin composition according to the present invention include a mercury vapor arc, a carbon arc, a Xe arc, and the like, which emit light having a wavelength of 250nm to 450nm, but are not limited thereto.
The resin composition according to the present invention may be used for a pigment dispersion type photosensitive material for manufacturing a color filter of a thin film transistor liquid crystal display (TFT LCD) device, a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display (TFT LCD) device or an organic light emitting diode, a photosensitive material for forming an overcoat layer, a column spacer photosensitive material, a photo-curable coating material, a photo-curable ink, a photo-curable adhesive, a printing plate, a photosensitive material for a printed circuit board, a photosensitive material for a Plasma Display Panel (PDP), etc., and uses thereof are not particularly limited.
An exemplary embodiment of the present invention provides a color filter including a photosensitive material.
The color filter can be manufactured by using a resin composition including a colorant composition. The color filter may be formed by applying a resin composition on a substrate to form a coating film, and exposing, developing and curing the coating film.
The resin composition according to one exemplary embodiment of the present invention has excellent heat resistance and thus a slight color change due to heat treatment, and thus, can provide a color filter having a high color gamut, high brightness, and contrast even if a curing process is performed when manufacturing the color filter.
The substrate may be a glass plate, a silicon wafer, and a plastic substrate material plate such as Polyethersulfone (PES) and Polycarbonate (PC), and the type thereof is not particularly limited.
The color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.
According to another exemplary embodiment, the color filter may further include an overcoat layer.
For the purpose of improving contrast, a lattice-like black pattern called a black matrix may be disposed between the color pixels of the color filter. Chromium may be used as a material of the black matrix. In this case, a method of depositing chromium over the entire glass substrate and forming a pattern by performing an etching process may be used. However, in consideration of high cost in the process, high reflectance of chromium, and environmental pollution caused by chromium waste water, the resin black matrix may be used by a pigment dispersion method, in which fine processing may be performed.
The black matrix according to an exemplary embodiment of the present invention may use a black pigment or a black dye as a colorant. For example, carbon black may be used alone, or a mixture of carbon black and a coloring pigment may be used, and in this case, since a coloring pigment having insufficient light-shielding property is mixed, there are advantages as follows: even if the amount of the colorant is relatively increased, the strength of the film or adhesion to the substrate is not deteriorated.
There is provided a display device including a color filter according to the present invention.
The display device may be any one of the following: plasma Display Panels (PDPs), Light Emitting Diodes (LEDs), Organic Light Emitting Diodes (OLEDs), Liquid Crystal Display (LCD) devices, thin film transistor-liquid crystal display (LCD-TFT) devices, and Cathode Ray Tubes (CRTs).
Hereinafter, the present invention will be described in detail with reference to examples. The following embodiments are provided to describe the present invention, and the scope of the present invention includes the scope described in the following claims and alternatives and modifications thereof, and is not limited to the scope of the embodiments.
Preparation example 1 preparation of chemical formula 1-1
1) Preparation of intermediate 3
Figure GDA0002043401260000291
25g (157.041mmol, 1 equiv.) of intermediate 1 was placed in 200g of dichloromethane (produced by Daejung Chemicals)&Materials co., ltd., manufactured), and the resulting mixture is stirred. An ice bath was provided to maintain the reaction solution at 0 deg.C, and 19.07g (188.454mmol, 1.2 equiv.) of triethylamine was slowly added dropwise to the reaction solution. Thereafter, 30.787g (174.321mmol, 1.11 equivalents) of intermediate 2 were slowly added dropwise to the reaction solution. The resulting mixture was allowed to react at 0 ℃ for 30 minutes, and then stirred at ordinary temperature for 24 hours. 300g of distilled Water (DI-Water) was added to the reaction solution, and the resulting mixture was stirred for 30 minutes, followed by separation of an organic layer and an aqueous layer. 200ml of MC was added to the separated aqueous layer and extracted additionally. The organic layer was placed in 200ml of 5% K2CO3In the solution, the resulting mixture was stirred, and then the organic layer was separated. Distilled water (DI water) was added to the organic layer and extraction was repeated until the solution was neutralized. The solvent was removed from the organic layer under reduced pressure. The precipitate was added to 500ml of Ethyl Acetate (EA) and n-hexane (n-Hex) (ratio of Ethyl Acetate (EA) to n-hexane (n-Hex) was 1:3), the resulting mixture was stirred and filtered under reduced pressure, and the precipitate was dried at 80 ℃ overnight to obtain 45.736g (152.79mmol) of intermediate 3 as a white solid. (yield: 97%)
1H NMR(500MHz,CDCl3):8.00～7.97(t,3H),7.70～7.68(d,1H),7.66～7.65(d,1H),7.59～7.55(t,1H),7.47～7.42(q,3H),7.21～7.20(d,1H),2.51(s,3H)
2) Preparation of chemical formula 1-1
Figure GDA0002043401260000292
1.32g (4.41mmol) of intermediate 3, 40.65g (4.41mmol) of intermediate A-1, 10g of benzoic acid and 10g of methyl benzoate were placed in a two-necked round-bottomed flask under nitrogen and the resulting mixture was stirred. The mixture was allowed to react at 150 ℃ for 5 hours. The reaction solution was slowly added dropwise to 200ml of methanol, and the resulting mixture was stirred for 1 hour. The precipitate was filtered under reduced pressure, washed with methanol, and then dried at 80 ℃ overnight to obtain 1.14g (2.56mmol) of chemical formula 1-1. (yield: 58.1g)
APCI + and M/z 430[ M + H ]]+And the accurate quality is as follows: 429
Preparation example 2 preparation of chemical formulas 1 to 2
The preparation was carried out in the same manner as in 2) of preparation example 1, chemical formula 1-1, except that the following intermediate A-2 was used instead of intermediate A-1.
Figure GDA0002043401260000301
Preparation example 3 preparation of chemical formulas 1 to 3
The preparation was carried out in the same manner as in 2) of preparation example 1, chemical formula 1-1, except that the following intermediate A-3 was used instead of intermediate A-1.
Figure GDA0002043401260000302
Preparation example 4 preparation of chemical formulas 1 to 4
The preparation was carried out in the same manner as in 2) of preparation example 1, chemical formula 1-1, except that the following intermediate A-4 was used instead of intermediate A-1.
Figure GDA0002043401260000311
Preparation example 5 preparation of chemical formulas 1 to 5
The preparation was carried out in the same manner as in 2) of preparation example 1, chemical formula 1-1, except that the following intermediate A-5 was used instead of intermediate A-1.
Figure GDA0002043401260000312
Preparation example 6 preparation of chemical formulas 1 to 6
The preparation was carried out in the same manner as in 2) of preparation example 1, chemical formula 1-1, except that the following intermediate A-6 was used instead of intermediate A-1.
Figure GDA0002043401260000313
Preparation example 7 preparation of chemical formulas 1 to 7
Figure GDA0002043401260000314
Under nitrogen, 1.32g (4.41mmol) of intermediate 3, 0.851g (4.41mmol) of intermediate A-7 and 10g of benzoic acid were placed in a two-necked round bottom flask and the resulting mixture was stirred. The mixture was allowed to react at 190 ℃ to 200 ℃ for 5 hours. The reaction solution was slowly added dropwise to 200ml of methanol, and the resulting mixture was stirred for 1 hour. The precipitate was filtered under reduced pressure, washed with methanol, and then dried at 80 ℃ overnight to obtain 0.802g (1.690mmol) of chemical formula 1-7. (yield: 38.3%)
APCI + and M/z 475M + H]+And the accurate quality is as follows: 474
Preparation example 8 preparation of chemical formulas 1 to 8
Preparation was carried out in the same manner as in preparation example 7 except that the following intermediate A-8 was used instead of intermediate A-7.
Figure GDA0002043401260000321
Preparation example 9 preparation of chemical formulas 1 to 9
Preparation was carried out in the same manner as in preparation example 7 except that the following intermediate A-9 was used instead of intermediate A-7.
Figure GDA0002043401260000322
Preparation example 10 preparation of chemical formulas 1 to 10
Preparation was carried out in the same manner as in preparation example 7 except that the following intermediate A-10 was used in place of intermediate A-7.
Figure GDA0002043401260000331
Preparation example 11 preparation of chemical formulas 1 to 11
Preparation was carried out in the same manner as in preparation example 7 except that the following intermediate A-11 was used instead of intermediate A-7.
Figure GDA0002043401260000332
Preparation example 12 preparation of chemical formulas 1 to 12
Preparation was carried out in the same manner as in preparation example 7 except that the following intermediate A-12 was used instead of intermediate A-7.
Figure GDA0002043401260000333
Preparation example 13 preparation of chemical formulas 1 to 13
Preparation was carried out in the same manner as in preparation example 7 except that the following intermediate A-13 was used instead of intermediate A-7.
Figure GDA0002043401260000341
Preparation example 14 preparation of chemical formulas 1 to 14
Preparation was carried out in the same manner as in preparation example 7 except that the following intermediate A-14 was used instead of intermediate A-7.
Figure GDA0002043401260000342
Preparation example 15 preparation of chemical formulas 1 to 15
Preparation was carried out in the same manner as in preparation example 7 except that the following intermediate A-15 was used instead of intermediate A-7.
Figure GDA0002043401260000343
Preparation example 16 preparation of chemical formulas 1 to 16
Preparation was carried out in the same manner as in preparation example 7 except that the following intermediate A-16 was used instead of intermediate A-7.
Figure GDA0002043401260000351
Preparation example 17 preparation of chemical formulas 1 to 17
Preparation was carried out in the same manner as in preparation example 7 except that the following intermediate A-17 was used in place of intermediate A-7.
Figure GDA0002043401260000352
Preparation example 18 preparation of chemical formulas 1 to 18
Preparation was carried out in the same manner as in preparation example 7 except that the following intermediate A-18 was used instead of intermediate A-7.
Figure GDA0002043401260000353
Preparation example 19 preparation of chemical formulas 1 to 19
Preparation was carried out in the same manner as in preparation example 7 except that the following intermediate A-19 was used instead of intermediate A-7.
Figure GDA0002043401260000354
Preparation example 20 preparation of chemical formulas 1 to 20
Figure GDA0002043401260000361
1.32g (4.41mmol) of intermediate 3, 0.874g (4.41mmol) of intermediate A-20, 10g of benzoic acid and 10ml of methyl benzoate were placed in a two-necked round-bottomed flask under nitrogen and the resulting mixture was stirred. The mixture was allowed to react at 190 ℃ to 200 ℃ for 5 hours. The reaction solution was slowly added dropwise to 200ml of methanol, and the resulting mixture was stirred for 1 hour. The precipitate was filtered under reduced pressure, washed with methanol, and then dried at 80 ℃ overnight to obtain 0.602g (1.350mmol) of chemical formula 1-20. (yield: 30.6%)
The ionization mode is APCI +: M/z is 480[ M + H]+And the accurate quality is as follows: 479
Preparation example 21 preparation of chemical formulas 1 to 21
Preparation was carried out in the same manner as in preparation example 20 except that the following intermediate A-21 was used in place of intermediate A-20.
Figure GDA0002043401260000362
Preparation example 22 preparation of chemical formulas 1 to 22
Preparation was carried out in the same manner as in preparation example 20 except that the following intermediate A-22 was used in place of intermediate A-20.
Figure GDA0002043401260000371
Preparation example 23 preparation of chemical formulas 1 to 23
Preparation was carried out in the same manner as in preparation example 20 except that the following intermediate A-23 was used instead of intermediate A-20.
Figure GDA0002043401260000372
Preparation example 24 preparation of chemical formulas 1 to 24
Preparation was carried out in the same manner as in preparation example 20 except that the following intermediate A-24 was used in place of intermediate A-20.
Figure GDA0002043401260000373
Preparation example 25 preparation of chemical formulas 1 to 26
Preparation was carried out in the same manner as in preparation example 20 except that the following intermediate A-26 was used in place of intermediate A-20.
Figure GDA0002043401260000381
Example preparation of resin composition
The resin compositions in examples 1 to 4 were prepared by using the contents described in table 1 below.
Intermediates 1,2 and a-1 to a-23 used in the preparation examples were purchased from Sigma-Aldrich and used.
[ Table 1]
Figure GDA0002043401260000382
Manufacturing a substrate
The resin compositions prepared in examples 1 to 4 were spin-coated on glass (5cm × 5cm), and subjected to a preheating treatment (prebaking) at 100 ℃ for 100 seconds to form a film. The interval between the substrate on which the film was formed and the photomask was set to 250 μm, and 40mJ/cm was irradiated on the entire surface of the substrate using an exposure apparatus2The amount of exposure.
Thereafter, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds and subjected to a post heat treatment (post bake) at 230 ℃ for 20 minutes, thereby producing a substrate.
Evaluation of Heat resistance
A spectrometer (MCPD manufactured by Otsuka Electronics co., ltd.) was used to obtain an absorption spectrum in the visible light region in the visible light range of 380nm to 780nm from the post-heat-treated (post-bake once (PB once)) substrate manufactured under the above conditions. Further, the pre-heat treated (pre-bake (prB)) substrate was additionally post-heat treated (post-bake (PB)) at 230 ℃ for 20 minutes to obtain a transmission spectrum from the same apparatus and measurement range.
Using the obtained absorption spectrum and a C light source backlight, Eab was calculated using the obtained values E (L, a, b), and the calculated values are shown in table 2 below.
ΔE(L*,a*,b*)＝{(ΔL*)2+(Δa*)2+(Δb*)2}1/2
A small value of Δ E indicates excellent color heat resistance.
When the value of Δ E is less than 3, the resulting product can be used as a coloring matter of a color filter.
The measurement results of the heat resistance are shown in table 2. As shown in table 2, it was confirmed that the color change (Δ Eab) of the compounds applied to examples 1 to 3 was less than 3.
Further, FIG. 1 shows the absorption spectrum in the visible light region of a substrate made of the resin composition of example 1,
FIG. 2 shows an absorption spectrum in the visible light region of a substrate made from the resin composition in example 2, an
Fig. 3 shows an absorption spectrum in the visible light region of a substrate made of the resin composition in example 3.
[ Table 2]
Delta Eab (post heat treatment-preheating treatment)
Example 1 2.84
Example 2 0.87
Example 3 0.26

Claims (10)

1. A compound represented by the following chemical formula 1:
[ chemical formula 1]
Figure FDA0002298780210000011
In the chemical formula 1, the first and second,
y is a direct bond or CQ1Q2,
r1 to R5, R10 to R14, Q1 and Q2 are the same or different from each other and each independently hydrogen, deuterium, or an alkyl group having 1 to 30 carbon atoms,
r6 to R9 are the same as or different from each other and are each independently hydrogen, deuterium, a halogen group, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms,
or
At least one of Q1, Q2, and R6 to R14 and an adjacent group are bonded to each other to form a benzene ring or a naphthalene ring, which are substituted or unsubstituted with a nitro group.
2. The compound according to claim 1, wherein chemical formula 1 is represented by the following chemical formula 1-a or 1-b:
[ chemical formula 1-a ]
Figure FDA0002298780210000012
[ chemical formula 1-b ]
Figure FDA0002298780210000021
In chemical formulas 1-a and 1-b, R1 to R14, Q1 and Q2 are defined as those in chemical formula 1.
3. The compound of claim 1, wherein chemical formula 1 is represented by any one of the following chemical formulae:
Figure FDA0002298780210000022
Figure FDA0002298780210000031
Figure FDA0002298780210000041
Figure FDA0002298780210000051
Figure FDA0002298780210000061
4. a colorant composition comprising the compound according to any one of claims 1 to 3.
5. The colorant composition of claim 4, further comprising:
at least one of a dye and a pigment.
6. A resin composition comprising:
a compound according to any one of claims 1 to 3;
a binder resin;
a polyfunctional monomer;
a photoinitiator; and
a solvent.
7. The resin composition according to claim 6, wherein the resin composition comprises, based on the total weight of the solid content in the resin composition,
the content of the compound represented by chemical formula 1 is 0.1 to 60% by weight,
the content of the binder resin is 1 to 60% by weight,
the photoinitiator is present in an amount of 0.1 to 20 wt%, and
the multifunctional monomer is contained in an amount of 0.1 to 50 wt%.
8. A photosensitive material prepared by using the resin composition according to claim 6.
9. A color filter comprising the photosensitive material according to claim 8.
10. A display device comprising the color filter according to claim 9.
CN201611042509.8A 2015-11-24 2016-11-23 Compound, colorant composition comprising the compound, and resin composition comprising the compound Active CN106957263B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2015-0164880 2015-11-24
KR20150164880 2015-11-24

Publications (2)

Publication Number Publication Date
CN106957263A CN106957263A (en) 2017-07-18
CN106957263B true CN106957263B (en) 2020-06-05

Family

ID=58817814

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201611042509.8A Active CN106957263B (en) 2015-11-24 2016-11-23 Compound, colorant composition comprising the compound, and resin composition comprising the compound

Country Status (4)

Country Link
JP (1) JP6604606B2 (en)
KR (1) KR102035893B1 (en)
CN (1) CN106957263B (en)
TW (1) TWI682924B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102131992B1 (en) * 2017-04-13 2020-07-08 주식회사 엘지화학 Compound and photo-sensitive resin composition comprising the same
KR102237127B1 (en) * 2018-02-26 2021-04-06 주식회사 엘지화학 Compound, colorant composition comprising the same and resin composition comprising the same
KR102314483B1 (en) * 2018-06-22 2021-10-19 주식회사 엘지화학 Compound, polymer, colorant composition, resin composition, color filter and display device
TW202231641A (en) 2020-12-16 2022-08-16 日商富士軟片股份有限公司 Composition, membrane, optical filter, solid image pickup element, image display apparatus, and infrared ray sensor
EP4266093A4 (en) 2020-12-17 2024-08-28 Fujifilm Corp Composition, film, optical filter, solid-state imaging element, image display device, and infrared sensor

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3932419A (en) * 1972-05-27 1976-01-13 Bayer Aktiengesellschaft Quinophthalone dyestuffs
JP2003176308A (en) * 2001-12-11 2003-06-24 Mitsubishi Chemicals Corp Dye-containing resin fine particle and dispersion thereof
JP2008094873A (en) * 2006-10-06 2008-04-24 Toyo Ink Mfg Co Ltd Pigment dispersant, pigment composition and pigment dispersion
JP2014035351A (en) * 2012-08-07 2014-02-24 Toyo Ink Sc Holdings Co Ltd Colored composition for color filter, and color filter
JP2014085565A (en) * 2012-10-25 2014-05-12 Toyo Ink Sc Holdings Co Ltd Colored composition for color filter and color filter
JP2014193955A (en) * 2013-03-28 2014-10-09 Toyo Ink Sc Holdings Co Ltd Quinophthalone compound and coloring composition containing the same
JP2015175927A (en) * 2014-03-14 2015-10-05 東洋インキＳｃホールディングス株式会社 Colored composition for color filter, and color filter

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS529029A (en) * 1975-07-05 1977-01-24 Bayer Ag Quinophthalone dyes
JPH06145146A (en) * 1992-11-06 1994-05-24 Chisso Corp Oxinate derivative
KR20010009058A (en) 1999-07-07 2001-02-05 성재갑 Photosensitive resin composition
KR101745062B1 (en) * 2013-11-29 2017-06-09 주식회사 엘지화학 Resin composition, photosensitive material, color filter and display appratus
KR101688011B1 (en) * 2014-01-14 2016-12-20 제일모직주식회사 Photosensitive resin composition and color filter using the same

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3932419A (en) * 1972-05-27 1976-01-13 Bayer Aktiengesellschaft Quinophthalone dyestuffs
JP2003176308A (en) * 2001-12-11 2003-06-24 Mitsubishi Chemicals Corp Dye-containing resin fine particle and dispersion thereof
JP2008094873A (en) * 2006-10-06 2008-04-24 Toyo Ink Mfg Co Ltd Pigment dispersant, pigment composition and pigment dispersion
JP2014035351A (en) * 2012-08-07 2014-02-24 Toyo Ink Sc Holdings Co Ltd Colored composition for color filter, and color filter
JP2014085565A (en) * 2012-10-25 2014-05-12 Toyo Ink Sc Holdings Co Ltd Colored composition for color filter and color filter
JP2014193955A (en) * 2013-03-28 2014-10-09 Toyo Ink Sc Holdings Co Ltd Quinophthalone compound and coloring composition containing the same
JP2015175927A (en) * 2014-03-14 2015-10-05 東洋インキＳｃホールディングス株式会社 Colored composition for color filter, and color filter

Also Published As

Publication number Publication date
JP6604606B2 (en) 2019-11-13
KR102035893B1 (en) 2019-10-29
JP2017095706A (en) 2017-06-01
CN106957263A (en) 2017-07-18
TW201733987A (en) 2017-10-01
KR20170060579A (en) 2017-06-01
TWI682924B (en) 2020-01-21

Similar Documents

Publication Publication Date Title
CN107488159B (en) Compound, colorant composition comprising the same, and resin composition comprising the same
CN107033077B (en) Compound, colorant composition comprising the same, and resin composition comprising the same
CN106957263B (en) Compound, colorant composition comprising the compound, and resin composition comprising the compound
TWI675830B (en) Xanthene-based compound, colorant composition comprising the same and resin composition comprising the same
KR101997656B1 (en) Xanthene-based compound and photosensitive resin composition comprising the same
CN104768925B (en) The compound of styrene-based base and its application in coloured material, photosensitive resin, photoresist, color filter and display device
CN107656423B (en) Photosensitive resin composition and color filter containing the same
JP6562470B2 (en) COMPOUND, COLOR MATERIAL COMPOSITION CONTAINING THE SAME AND RESIN COMPOSITION CONTAINING THE SAME {COMPUND, COLORANT COMPOSION COMPRISING THE SAME AND RESIN COMPOSITION COMPRISING THE SAME}
CN109312170B (en) Compound and photosensitive resin composition comprising the same
JP6897906B2 (en) Compounds, color material compositions containing them, and resin compositions containing them
CN107759557B (en) Compound, colorant composition containing the same, and resin composition containing the same
KR101745062B1 (en) Resin composition, photosensitive material, color filter and display appratus
JP6631861B2 (en) Compound, coloring material composition containing the same and resin composition containing the same
KR20170009099A (en) Compound, colorant composition comprising the same and resin composition comprising the same
KR102016619B1 (en) Novel compound, colorant composition comprising the same and resin composition comprising the same
KR102683195B1 (en) Colorant composition, photosensitive resin composition, photo resist, color filter, and display device
TWI714122B (en) Compound, polymer, colorant composition, resin composition, color filter and display device
KR101747528B1 (en) Indole-based compound, colorant composition comprising the same and resin composition comprising the same
TW202024243A (en) Photosensitive resin composition, photoresist, color filter and display device

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant